Multi-substituent psilocybin derivatives and methods of using

Abstract

Disclosed are novel multi-substituent psilocybin derivative compounds and pharmaceutical and recreational drug formulations containing the same. The compounds may be produced by reacting a reactant psilocybin derivative with a substituent containing compound.

1 . A chemical compound or a salt thereof having a formula (I): 
       
         
           
           
               
               
           
         
       
       wherein, at least two of R 2 , R 4 , R 5 , R 6 , or R 7  are substituents independently selected from at least two of (i) a halogen atom, (ii) a hydroxy group, (iii) a nitro group, (iv) a glycosyloxy group, (v) an amino group or an N-substituted amino group, (vi) a carboxyl group or a carboxylic acid derivative, (vii) an aldehyde or a ketone group, (viii) a prenyl group, and (ix) a nitrile group, and wherein each non-substituted R 2 , R 5 , R 6 , or R 7  is a hydrogen atom and when R 4  is not substituted with any of the foregoing substituents, R 4  is a hydrogen atom, an O-alkyl group, an O-acyl group, or a phosphate group, and wherein R 3a  and R 3b  are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an acyl group, or an aryl group, and R 3c  is a hydrogen atom or a carboxyl group. 
     
     
         2 . A chemical compound according to  claim 1 , wherein chemical compound (I) is selected from a compound having a chemical formula (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), (XVII), (XVIII), (XIX), (XX), (XXI), (XXII), (XXIII), (XXIV), (XXV), (XXVI), (XXVII), (XXVIII), (XXIX), (XXX), (XXXI), (XXXII), (XXXIII), (XXXIV), (XXXV), (XXXVI), (XXXVII), (XXXVIII), (XXXIX), (XL), (XLI), (XLII), (XLIII), (XLIV), (XLV), (XLVI), (XLVII), (XLVIII), (XLIX), (L), (LI), (LII), (LIII), (LIV), (LV), (LXXVI), (LXXIX), (LXXX), (LXXXI), (LXXXII), (LXXXIII), (LXXXIV), (LXXXV), (LXXXVI), (LXXXVII), (LXXXVIII), and (LXXXIX): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         3 . A method for treating a psychiatric disorder, the method comprising administering to a subject in need thereof a pharmaceutical formulation comprising a chemical compound or a salt thereof having a formula (I): 
       
         
           
           
               
               
           
         
       
       wherein, at least two of R 2 , R 4 , R 5 , R 6 , or R 7  are substituents independently selected from at least one of each of (i) a halogen atom, and (ii) a prenyl group, and wherein each non-substituted R 2 , R 5 , R 6 , or R 7  is a hydrogen atom, and when R 4  is not substituted with any of the foregoing substituents, R 4  is a hydrogen atom, an O-alkyl group, an O-acyl group, or a phosphate group, and wherein R 3a  and R 3b  are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an acyl group, or an aryl group, and R 3c  is a hydrogen atom. 
     
     
         4 . A method according to  claim 3 , wherein in the chemical compound having formula (I), two of R 2 , R 4 , R 5 , R 6 , or R 7  are substituted. 
     
     
         5 . A method according to  claim 3 , wherein in the chemical compound having formula (I), two of R 5 , R 6 , and R 7  are substituted, and wherein R 2  and R 4  are hydrogen atoms. 
     
     
         6 . A method according to  claim 3 , wherein in the chemical compound having formula (I), R 5  and R 6  are substituted, and wherein R 2 , R 4 , and R 7  are hydrogen atoms. 
     
     
         7 . A method according to  claim 6 , wherein in the chemical compound having formula (I), R 5  is a halogen atom, and R 6  is a prenyl group. 
     
     
         8 . A method according to  claim 3 , wherein in the chemical compound having formula (I), the halogen atom is a fluorine atom. 
     
     
         9 . A method according to  claim 7 , wherein in the chemical compound having formula (I), the halogen atom is a fluorine atom. 
     
     
         10 . A method according to  claim 7 , wherein in the chemical compound having formula (I), R 3a  is a hydrogen atom and R 3b  is a (C 1 -C 3 )-alkyl group. 
     
     
         11 . A method according to  claim 7 , wherein in the chemical compound having formula (I), R 3a  is a hydrogen atom and R 3b  is a methyl group (—CH 3 ). 
     
     
         12 . A method according to  claim 7 , wherein in the chemical compound having formula (I), R 3a  and R 3b  are a (C 1 -C 3 )-alkyl group. 
     
     
         13 . A method according to  claim 7 , wherein in the chemical compound having formula (I), R 3a  and R 3b  are a methyl group (—CH 3 ). 
     
     
         14 . A method according to  claim 7 , wherein in the chemical compound having formula (I), R 3a  and R 3b  are a hydrogen atom. 
     
     
         15 . A method according to  claim 9 , wherein in the chemical compound having formula (I), R 3a  is a hydrogen atom and R 3b  is a (C 1 -C 3 )-alkyl group. 
     
     
         16 . A method according to  claim 9 , wherein in the chemical compound having formula (I), R 3a  is a hydrogen atom and R 3b  is a methyl group (—CH 3 ). 
     
     
         17 . A method according to  claim 9 , wherein in the chemical compound having formula (I), R 3a  and R 3b  are a (C 1 -C 3 )-alkyl group. 
     
     
         18 . A method according to  claim 9 , wherein in the chemical compound having formula (I), R 3a  and R 3b  are a methyl group (—CH 3 ). 
     
     
         19 . A method according to  claim 9 , wherein in the chemical compound having formula (I), R 3a  and R 3b  are a hydrogen atom. 
     
     
         20 . A method according to  claim 3 , wherein the compound having formula (I) is a compound having a chemical formula (A): 
       
         
           
           
               
               
           
         
       
       or a salt thereof.